Dimethylformamide → HCID 86741478, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.268 g (1 mM) of Nα-benzyloxycarbonyl-4-hydroxy-L-allothreoninamide in 5 mL DMF was cooled to -10° C. and 0.12 g (1 mM) chloroacetylisocyanate was added and the reaction was stirred at -10° C. for 1 hr to give (2S,3S)-2-benzyloxy-carboxamido-3-hydroxy-4-(N-chloroacetylcarbamoyloxy-butanamide. To the above reaction mixture, 0.148 g (1.25 mM) methanesulfonylchloride was added at -15° to -10° C. and 0.26 mL triethylamine was added subsequently. The reaction mixture was stirred at -15° to -10° C. for 40 min. After the reaction, ethylacetate (20 mL) was added. The resulting mixture was washed with 5% aqueous NaH2PO4, brine and the organic layer was dried over Na2SO4. Solvent was removed at the reduced pressure and the crude product was purified by column chromatograph (SiO2, EtOAc:Hexane-8:2) to give (2S, 3S)-2-benzyloxycarboxamido-3-methanesulfonyloxy-4-(N-chloroacetylcarbamoyloxy)-butanamide 0.25 g (53%).

Provenance & Evidence